Struggle of Surrender
by Fenikkusu Ai
Summary: Dean has never been helpless. Alastair changes that. Rated for mentions of torture and possible slash. Written for 10 hurt comfort.
1. Introductions

Title: Introductions

Author: Fenikkusu Ai

Claim: Alastair/Dean

Table: DIY

Prompt: #1 Cold

Rating: M

Summary: It wasn't supposed to be this cold in hell.

Word Count: 709

* * *

It wasn't supposed to be this cold in hell. Hell was supposed to be _hot_. Even that couldn't be counted on.

"Sam!" he screamed into the void for what could have been the thousandth time. There was no answer of course. Sam was somewhere above in the world of the living.

The icy winds whipped around Dean's defenseless body; rattling the chains that bound him hand and foot. He was helpless. For the first time in his life, he was helpless.

He was the fly caught in the spider's magnificent web. Like the ripe fruit hooked onto a tree limb waiting to be picked. He was the Hanged Man swinging from a rope.

In time, the spider came.

"Ooh, is this for me?"

Dean looked up to see a tall demon leering at him from above. The being's unusual flame white eyes appraised him wickedly. This demon was old. Ancient. He didn't need Sammy's research to confirm that.

"Am I yours? Your new little bitch?" Dean croaked.

The demon grinned sadistically. "Now, what do you think?"

Dean found himself strapped horizontally down to a table. The demon was chaining him down, and Dean didn't even bother struggling. He was too weak. Too drained.

"My name is Alastair, and I will be your torturer for eternity," it said in its nauseating lisp.

He closed his eyes and waited. He knew what was coming next. The unending agony.

"Open those peepers, Dean," the being crooned.

Dean choked back a scream when his mind registered the silver sickle.

"Shiny," he manages.

The demon fondled it fondly. "Isn't it? It's my favorite. Delicate for the smallest of cuts yet rougher when it needs to be. Yanks through the flesh like butter."

Alastair lowered the knife out of view. "Now, Dean, you're what is considered...a special case. You're not like every other evil shitbag who waltzes in the gate that deserves what's coming to them. You sold your soul to save your brother. A _righteous_ man." He smiled as if these words in particular were amusing.

"So? What's your big sales pitch?" Dean quipped; the chains biting into his wrists.

Alastair leaned in closer. "Stand beside me. Take my blade so I don't have to use it on you. Punish other souls."

It was far a far worse fate than he had imagined. Dean shivered in his chains. The cold was filling his very soul.

_Become a monster?_

"No thanks."

The demon's "nice" act disappeared with a flash of bared teeth. "Think you're acting so brave, boy?"

In one sharp movement, the cold sickle invaded Dean's stomach. Dots danced in front of his eyes as the pain manifested. He grunted slightly. The demon didn't seem very surprised and instead sighed dramatically.

"Hmm. You're going to be a tough nut to crack, aren't you? Like your daddy?

Dean jerked his head up in interest; ignoring the pain. "My dad? How...-"

Alastair brandished the sickle before bringing it up close to Dean's face. "I ask the questions here, Deano. You'll learn that soon enough."

The ensuing torture forced Dean into silence. The knife skimmed through his skin like a shark. Dean endured it; jaw locked tight. He wouldn't give this sonofabitch the satisfaction of screaming.

"Your resolve is impressive, but let's face it, Dean." Alastair's voice dropped to a whisper. "Everyone has their limit."

And Alastair tried his best to find it. Cutting, slicing, and filleting until Dean's world became pure pain. His vision eventually grew dark, and he had a precious moment of peace before he was blinking up at his torturer yet again.

"Welcome back, Dean. Are you surprised to be whole again?"

He licked his lips. Felt his stomach sink. "I can't die."

"You are dead after all, dear boy. And, I can keep bringing you back to life. Want to test me? Keep saying no. Now, will you take my most generous offer?"

He twisted in his chains. "Fuck you," Dean spat.

"You're going to be a fun one, Dean." It sounded like a promise.

Dean felt the sickle enter his flesh again.

The blade was cold.


	2. One Little Word

Title: One Little Word

Author: fennikusu_ai

Claim: Alastair/Dean

Table: DIY

Prompt: #2 Reputation

Rating: M

Summary: Only someone of his caliber, his reputation, could work on a soul such as Dean's.

Word Count: 431

* * *

Dean closed his startling wood green eyes. He kept his eyes closed much of the time. Such a nasty habit. Alastair wanted the young Winchester to be fully aware of the ravages he was inflicting on his body. Dean's lips moved silently, but no audible words could be heard.

"Whatever are you saying, dear boy? Are you thinking of me?" He kept his tone playful.

The muffled swear Alastair _did_ hear.

Disrespect was one thing he did not tolerate. His nostrils flared in anger as he ripped the knife straight across Dean's chest in a deep oozing gash prompting the boy to shriek and jerk against the restraints.

"You twisted bastard!" he roared at his torturer.

Alastair was sure the scream was heard all over hell. Perfect. Ever since John Winchester escaped from the pit without breaking, some of his fellow brood peevishly questioned his methods. The event had dented his reputation, and down here, reputation was everything. Reputation was the difference between being a slave or a master, and it had been several millennia since he had been at the bottom.

Alastair brought his lips close to Dean's ear. "Are you deliberately trying to test my patience?" he purred.

Dean shuddered. In revulsion.

"You know, there's only one way to stop our little game. One little word. I can't say it for you."

Dean whimpered.

"End it," Alastair whispered before dragging his tongue across the soul's cheek. "End the pain. Become my pupil."

The boy focuses his gaze on him. Parts his lips...

_Is this it?_

The demon waits in anticipation.

Alastair dodges the gob of spit. The boy was getting too predictable. A well aimed punch to the jaw reasserts dominance, but he is ultimately disappointed. He thought he had been getting somewhere.

Hell's executioner glowered down at his prey. Only someone of his caliber, his reputation, could work on a soul such as Dean's. Many other demons would have ripped him into unworkable shreds by now.

"Now, then. Your fingernails are getting a bit too long. They've grown back again."

The look of anguish on Dean's face is priceless. He mewls like a kitten when Alastair seizes his hand, but he does not beg. With vicious pleasure, Alastair sets the pliers on the right forefinger.

Dean is beyond beautiful when he is in pain. The way he writhes, wriggles, and squirms with his head tossed back in agony. Pretty whimpers escape his lips.

"By the way, Happy Anniversary, Dean."

This evening marked two wonderful years that they had been together.


	3. Home

Title: Home

Author: Fenikkusu Ai

Claim: Alastair/Dean

Table: DIY

Prompt: #3 Just Say No

Rating: M

Summary: Dean's mind is his only escape.

Word Count: 372

* * *

Dean flitted in and out of consciousness; Alistair's rasping voice in his ear.

"Come now, Dean," Alastair said with a chuckle. "It's been over seventeen years. Now, will you come off the rack like a good boy?"

His mouth was as dry as ash and caked with blood. "No."

Some days, he didn't even recognize his own voice anymore.

Alastair sighed. "Stubbornness. Kids these days. They never do as they're told."

In precious moments like these, Dean dissociated deep into his mind. Sometimes, there was just blackness waiting for him. Other times, there was a man with a sweep of dark hair, twinkling eyes, and a wide smile hiding there. Sam. His brother.

He wanted to go home. Wherever home was. Home with Sam. That sounded like a nice idea as the wicked knife dug into his cheekbone. The knife was merciful. Last time, Alastair had simply set him on fire until he burnt to a cinder. Alastair kept him on his toes. He was a creative fiend. And, Dean was simply a pathetic creature that was running out of quips and jibes to keep his spirit strong.

Only one small thought kept the engine of his body going.

_Just say "no." Keep telling him "no." "No" is the only word he needs to hear. "No" buys another day..._

But, the price was becoming high.

Alastair was a bad demon. The worst. Where Dean would use a slingshot, Alastair would use a tank. Alastair re-patterned himself after every encounter, every struggle, and every verbal attack. He adjusted himself to every strength, fault, and weak point Dean had. Dean's psyche was perpetually at war as one day stretched into the next.

Each and every time they tangled, Alastair would get closer into his mind. Into his soul. Soon, Dean's being would be devoured completely.

"You keep me young, Dean," Alastair confided in a whisper.

Soon, Dean's screaming was the only sound that filled the air with a new thought in his mind.

_Sam..._

_Why can't you save me?_


	4. Enough

Title: Enough

Author: Fenikkusu Ai

Claim: Alastair/Dean

Table: DIY

Prompt: #4 Broken

Rating: M

Summary: Dean looked up at his new master as a broken thing.

Word Count: 306

* * *

Today was the day. Dean knew it. He was trembling as Alastair approached him.

Alastair whistled. "Looky here. You've lasted thirty years. Someone's looking to set a new record."

Sometimes Dean thought he heard his father's voice urging him to be strong. But most of the time he just heard his own screams. He was...breaking. He'd known it for a while.

It was on his lips to say, "yes." Instead, he said...

"Please," he whimped pathetically in a tone he'd never known he could use.

Alastair frowned disapprovingly at his soon-to-be student. " 'Please' isn't the right word, Dean. You should know better by now."

He did know better. Dean just wanted to delay the inevitable.

"Now...where were we? Oh, yes. Cleaning my tools. You got them exceptionally dirty last time."

_No more._

Dean squirmed as a approached him with a knowing smirk on his face. His muscles were on fire. His mind was in shreds. His nerves were frayed to the ends. His tolerance was at its peak. He had had enough.

There was a bulge in his throat. He didn't want to say the words. He didn't want this to end. Yes, he wanted the torture to end, but not like this.

Alastair approached closer...

_He knows already._

"Yes," Dean panted.

Alastair stopped moving. The smile was frozen on his lips.

"Yes," Dean repeated while hating himself all the while. "Sign me up."

Alastair leered malevolently over him.

"Release," the demon ordered.

The chains unlocked and slid off Dean's body. He was finally free after thirty years.

Dean looked up at his new master as a broken thing.


	5. Daddy

Title: Daddy

Author: Fenikkusu Ai

Claim: Alastair/Dean

Table: DIY

Prompt: #5 Warm

Rating: M

Summary: Sarcasm even existed in hell.

Word Count: 263

* * *

He cried. He cried like he had never cried before.

Dean Winchester bawled like a baby before the demon torturer. With one word, he had lost this cruel game. A hunter...surrendering to a _demon_. But, then, the rules in hell were different from the ones on earth.

"Shhh. Let it out. Let it out. You'll feel much better," Alastair soothed.

Dean squeezed his eyes shut and sobbed.

He was now the demon's property. The demon's bitch. From now until eternity. How could he feel better?

Sarcasm even existed in hell.

Dean soon found himself being lifted into Alastair's uncomfortable, awkward embrace. The demon was warm. Warmth. Warmth at last. The heat was soaking into him. A warm body to hold onto after all this time. It was as if the demon had a core of fire.

It was comforting. So comforting...

"Shhh. It's all right. They'll be no more pain now. You just made me very proud today, Dean," the demon said in a honeyed yet emotionless tone. "My big boy, he whispered.

Dean was ashamed to find his arms wrap his torturer for support. He was so weak and Alastair was supporting him; holding him like a child. How far he'd sunk. How low could he still go?

The demon's hand stroked Dean's hair as his body went slack.

"It's all right," Alastair repeated. "_Daddy's_ got you."

Dean cried louder.

There was no escape now.


	6. Beautiful Boy

Title: Beautiful Boy

Author: Fenikkusu Ai

Claim: Alastair/Dean

Table: DIY

Prompt: #6 Torture

Rating: M

Summary: Sometimes, Dean wishes that he was back on the rack.

Word Count: 454

* * *

Dean's hand hesitated over the tools; fingers scrabbling at the empty air. He didn't want to do this anymore.

Alastair was at his side. Alastair was _always_ at his side. The bastard never left it.

"A new knife perhaps? Something easier?"

"No..." The word came out as a moan.

"A scalpel? Something smaller for the more delicate places?"

Dean stepped away from the torture instruments. He didn't want a one of them. Immediately, Alastair's arm shot out and brought him close again.

"Choose something, dear boy. Or, I promise you, I _will_." The threat hung in the air.

Dean glanced over at the soul on the rack. A young girl. Far too young. A suicide. It was his job to punish her. Alastair expected him to punish her until she screamed and begged for mercy. Until she broke. Just like he had. Except for her, there would be no reprieve. No offer to end her suffering.

Dean scowled and picked up a large ridged knife. Something new to please Alastair. All the torture instruments would hurt more or less anyway.

"Very nice. A little advanced though, but you'll have to learn how to handle all the equipment eventually. We'll consider it a practice session."

Dean suppressed the shudder that raced through his body. It would never end. This would continue. Forever.

The soul began to moan. "No more...no more..."

"Ignore her," Alastair hissed sharply. "Now, start. Or, I'll start on you all over again."

Suppressing a scream of rage, Dean sliced the girl's arm. He hated how she thrashed around like a fish and whimpered in an agony that would never end. Such a pathetic scene. He had been that way once, but there was a difference now. Now, he held the knife. And, down here, the knife meant power.

"Good boy. I knew you'd listen. Stay on my good side if you want your existence to be easy, Dean

Dean began to methodically rip the soul apart. As he did so, Alastair whispered advice into his ear on where to press the blade. How to make the process hurt more. Twisting his mind into the sick monster that he was.

"My boy. My beautiful boy. Molded into my image." Alastair sounded as pleased as any father.

He almost jumped out of his skin when ever so slightly Alastair's arms possessively wrapped around Dean's waist.

Dean lowered his head in resignation. He was feeling his resolve melt away. Soon, he would not only obey Alastair without question, he would willingly enjoy inflicting damage on the souls. It might take centuries, but it would happen.

Sometimes, Dean wishes that he was back on the rack.


	7. Exist

Title: Exist

Author: Fenikkusu Ai

Claim: Alastair/Dean

Table: DIY

Prompt: #7 Blood

Rating: M

Summary: If he surrendered, the pain stopped for a moment or two.

Word Count: 406

* * *

There was the blood. Always the blood everywhere. Dean could find no relief from it.

Hell was hurt. Hell was pain. The blood was endless. Red gore surrounded him everywhere. It trickled out of his victims to stain the floor crimson. It gushed down the walls and pooled around his feet. He could smell the rich iron odor of it in the air, taste it on his tongue, and most horribly feel it slide between his fingers.

_Drip, drip, drip..._

The sound was sickening.

In his life, Dean had seen plenty of blood. His own. His brother's. Demons and their victims. But, the blood would always stop. Wounds healed. Here, the wounds never closed. They continued to be cut fresh day after day.

Though employed under the master torturer, it wasn't all work. Even Dean had time off, but it was time spent under Alastair's watchful eye. He wasn't allowed to roam free. Not that there was an escape from hell.

On his knees, the place Alastair commanded him to be, Dean allowed his master to touch his property. Alastair's hand gently ruffled Dean's hair. He could literally feel the demon savor his submission. Dean bowed his head lower, and a fingers wound deeper into his hair. If he surrendered, the pain stopped for a moment or two. He could just...exist.

"You like me, don't you, Dean?"

Dean kept quiet. He knew Alastair wasn't expecting an answer anyway.

"I'll make you like me," the demon added lethally in a low whisper.

Dean gasped. Suddenly, he felt that he was suffocating. There was an ache in the pit of his stomach. Something bad was going to happen.

Then, the illusion of peace was shattered.

"You're just pretending!" With this last word, Alastair backhanded Dean across the face. The hunter slid across the floor into a pool of blood.

His cheek throbbed, and he knew Alastair had left a bruise. Dean just lay there and didn't make a move. He knew he would only make it worse.

Slowly, Alastair crept over. "You'll grow to like me, won't you, Dean? We have eternity after all. Soon, you'll beg for my touch. Won't you?"

"Yes, sir." It was as if Dean was speaking to his father again.

Alastair chuckled and Dean could glimpse the blood on his teeth. He could still hear the sound of blood dripping on the floor. The same repetitive sound.

_Drip...drip..._


	8. Crumbling

Title: Crumbling

Author: Fenikkusu Ai

Claim: Alastair/Dean

Table: DIY

Prompt: #8 Pet

Rating: M

Summary: He knew full well who was in charge here.

Word Count: 392

* * *

There was always something so satisfying about having a new pet.

"Dean?" Alastair called.

Obediently, the former hunter hurried to his side. He didn't even hesitate. Alertly, he stood there, and waited for further commands.

Alastair smiled at his charge. There was nothing that he needed. Except Deano's unwavering surrender.

Alastair laid a hand on the demon-in-training's shoulder. "Keep up the good work."

"Yes, sir." Dean nodded.

Alastair loved seeing the struggle in Dean's eyes. He could see two strong wills clashing in their viridian depths. A spark of rebellion remained, but it was slowly being cooled into a mellow acquiescence. Dean now knew disobedience meant pain. Punishment. But, surrender brought rewards. Quite a dilemma.

Alastair possessively slid a hand down Dean's arm. The boy flinched, but he stayed perfectly still. He knew better than to deny his master his property.

What a find Dean was. Alastair thought he had found a prize with John, but his son was better. So willing. So eager to please.

Struck with inspiration, Alastair seized Dean's chin. Slowly, gaugingly, he blazed a path up his chin with his fingers; eyes searching the boy's own. Dean gazed placidly back. He knew full well who was in charge here.

"Good," Alastair breathed.

It wouldn't be as long as he thought. Though, Dean had shown a great deal of resistance at the beginning, his will was slowly but surely crumbling away. Much faster than he anticipated. He was truly his father's son. No wonder John had had such an easy time controlling him.

Alastair's hand swept Dean's mouth. At this, Dean closed his eyes.

"There's no need to be frightened, sweetheart. It's only me after all."

To his delight, Dean began to sob. He watched in fascination as a tear escaped the corner of the boy's right eye.

"Come now, kiddo. There's some new arrivals that are as new as they come. Introduce th to eternity with your blade. That'll put a smile back on that face, won't it?"

The sarcasm was intentional.

Sooner rather than later, Alastair wanted Dean's eyes to turn from green to black.

Then, there would be no going back.


	9. Apt Pupil

Title: Apt Pupil

Author: Fenikkusu Ai

Claim: Alastair/Dean

Table: DIY

Prompt: #9 Seeing You With New Eyes/Second Look

Rating: M

Summary: He didn't blink.

Word Count: 579

A/N: Mentions of slash.

* * *

Dean looked up at his master. His father. His teacher. His god. He was making another tragic soul wail beautifully with his wicked knife. Dean now knew Alastair's favorite one.

It had been painful in the beginning. Those memories. They had gotten in the way of who he really was, and all it had taken was Alastair to carve it out. Dean had been a blank canvas. Now, he was filled with the most exquisite masterpiece ever created.

Dean sat at Alastair's feet and watched him work. He didn't blink. He didn't move. All he did was appreciate and learn.

Alastair truly was a master at torture. He knew everything. How many bones were in the human body, what the names of all the muscles were, and which ones were the most painful to snap. Dean watched in fascination as he learned technique after technique. He felt so privileged to be here now. So valued.

And Alastair always put on a show...

"I can feel you watching, Dean." Alastair lisped.

Dean jerked out of his reverie. His master was speaking.

"Would you like to do more than just watch?"

"I'm not very good yet." Dean bowed his head sheepishly.

"Practice, my boy. How will you get better without any practice?"

Alastair turned around with a broad smile. His hands dripped with blood. The soul he was working on whimpered in relief when her torturer shifted his focus. The demon advanced on Dean.

"You're warming up to me, aren't you?"

Dean helplessly nodded.

"Excellent," Alastair purred. "Get up."

He obeyed. Dean could feel Alastair appraising his investment from his head to his toes. He could feel the being's white eyes boring into his soul. There was nowhere to hide.

Once more, Dean was swept into Alastair's arms. He now knew that the master torturer thrived on touch. He craved it. Especially from his favorite student. Something inside of him should resist this. _Fight_. Something would have before. Now, Dean allowed Alastair's hands to run up and down his back in a disturbing rhythm.

"Shall we go?"

Dean allowed himself to be led to the suffering soul. Immediately, it began whimpering and struggling again.

"Here, boy." Alastair handed Dean the knife.

Without a thought, Dean did so and began working the soul over; following Alastair's previous handiwork as best he could. He was a perfect student. An apt pupil.

However, the soul's cries annoyed him. Made him angrier. Made his knife cut deeper and deeper...

He could feel his eyes grow intense in a black rage. They became harder. Sharper. More predatory than before.

"Shut up, you bitch!" he finally snapped at her. Didn't she know begging was useless? Made her even weaker?

"I think that's enough for today, Dean. You're getting overly excited."

It was almost merciful when the knife was taken away from Dean's trembling fingers. Sometimes, an unknown anger took over, and he just...lost control. Hesitantly, he looked up at his mentor; hungry for some sort of reaction.

"It happens sometimes in the beginning. You'll gain more control. You'll get better. I'll make sure of it," Alastair soothed.

Before Dean could take another breath, Alastair leaned in and trapped his lips with a kiss. The demon's tongue tasted like blood, despair, and arrogance.

They merged on the cold stone floor where Alastair claimed his property.

Dean Winchester was also turning into a perfect whore.


	10. Light

Title: Light

Author: Fenikkusu Ai

Claim: Alastair/Dean

Table: DIY

Prompt #10: Escape

Rating: M

Summary:

Word Count: 500

A/N: There will be a sequel. Thanks to all who reviewed, faved, and alerted. :)

* * *

Ten years had passed, and Alastair was most pleased. Dean was blossoming into his full potential. The boy had talent. He easily commanded authority, and he handled the knife like no other. It had been a while he had been so...close to his one of his students. Out of the lucky hundreds he'd personally trained over the centuries, Dean was one of his best.

The room was full of Dean's masterpieces. Now, he not only obeyed but enjoyed carving those anonymous souls up. Alastair watched on like a proud papa. An attentive lover.

Dean was smiling again. He joked. He laughed. All of that godawful brooding and transitional grief was done; a phase like an adolescent tantrum. The struggle was over, and he had won

"My funny boy." Alastair tongued his ear. "All mine."

Dean flashed a reckless grin and Alastair jeered back. It was a moment that could have passed as human affection if they were human. Dean's black eyes were proof of that. They suited him better than green ever could.

Then, the day arrived where it was all snatched away.

* * *

Dean was transfixed by the _light_. He stared into it, and it seemed to smile into his soul.

_Dean._

The word caressed his heart.

It knew his name. This diamond bright and gold radiance knew his name.

Suddenly, Dean began to weep as his sins were exposed. Somewhere in his soiled soul, the light opened a crack of remorse. He was...confused. Was he damned? Evil? Could he be forgiven?

Inside that peaceful glow was the outline of wings. He could feel the being within the brillance beaming at him.

_Dean, come with me now._

The command was surprisingly stern, but Dean was used to following orders. He followed the being—the angel—into the light and soon felt himself being ripped away once again to another dimension.

He left the shadows of hell and whatever lurked in them behind.

* * *

Alastair was _furious_. More furious than when Lucifer had fallen from grace, and that was hard to accomplish. He roared with rage until he was sure all of hell heard him; taking the knife Dean had left behind and mercilessly mutilating the teenaged soul he had been working on even after it was long dead.

What right did those smug, self-righteous, feathered pricks to take his boy? They had _purified_ him. His greatest project was ruined. And Dean had gone so willingly. But, Alastair wasn't surprised. Heaven had tricks of its own.

In hours, days, or weeks, Alastair gradually regained his composure. Deano was gone. He was now a living breathing man. All right. Alastair accepted that. Time for a change of plan.

But, Dean would be back. He'd started the apocoplypse after all.

And, Alastair wanted to be there in person to tell him...


End file.
